Dear Jack:

It sounds like you’re in a deeply reflective place, and I want to acknowledge how much growth you’ve undergone. Therapy has given you insight into your past wounds and patterns, and that alone is an incredible step forward.

There’s a lot to untangle here. On one hand, you’re drawn to reconnecting with your ex, now that you feel more equipped to nurture a healthier relationship. On the other, you’re feeling pulled toward new experiences—toward exploring connections you never got the chance to before. Both feelings are valid, and neither is wrong.

The truth is, reconciliation requires more than just personal growth—it also requires mutual readiness. If you reach out to your ex, it’s important to ask whether she still wants that relationship too, and if she’s in a place to reconnect. But before even getting there, the question is: Do you truly want to rekindle things for the right reasons, or are you feeling a mix of guilt, nostalgia, and uncertainty?

It’s also okay to acknowledge the curiosity you have about new experiences. If the desire for exploration feels like it would be a lingering regret, then that’s worth sitting with seriously. If you jump back into your past relationship, would that feeling dissolve, or would it eventually create resentment?

Sometimes, clarity comes when we slow down and let go of the pressure to act immediately. Maybe you don’t have to make a decision today—maybe the right answer will become clearer as you continue growing and healing.

At the end of the day, your journey is yours to define, and whatever path you choose should be one that aligns with what feels authentic to you. Whether that’s reaching out to your ex or stepping into the unknown, you deserve a relationship—past or future—that reflects the person you are becoming.

How does this sit with you?

anita

Dear Jack:

I want to give your post my full attention tomorrow morning (it’s Monday afternoon here). Please feel free to add anything you think is relevant before I get back to you.

anita

Dear jack

Congratulations on choosing to go into therapy & that it has brought you some understanding of how your past impacted upon the relationship you had with your ex.
It may be worthwhile to reach out to her in a letter saying that you went into therapy & what you discovered & apologize for the manner in which you separated. This way she can digest the information at a distance & gives her the opportunity to show whether she has any inclination towards friendship or reconciliation or even that she does not want you in her life at all.

From your side take note when she comes to mind, are you tired hungry lonely? or a location, a film etc that triggers things & what emotion is present ie you see something & you mentally go Ooh I must tell her about it, or you see an intimate scene in a film & it triggers lust for intimacy.
Along side this also see what attracts you when you see other women in passing their smile, walk. how animated & open they are etc just don’t be creepy about it – it only takes a glance, you could practice by scanning crowds ie waiting at a bus or train station. I remember sitting at a station cafe when a number of trains disembarked and all the people heads down disconnected from the world around them, reminded me of ants scurrying about, but there was one woman who walked head up with a bounce in her step our eyes met we smiled & acknowledged each other.
Kind regards
Roberta

Dear Jack:

You’ve done remarkable inner work to better understand yourself, and that’s truly something to celebrate. Therapy has given you clarity on your emotional wounds, past patterns, and what you genuinely want moving forward. That level of self-awareness is rare, and it will serve you well in whatever path you choose.

From what you’ve shared, your desire to reconnect with your ex seems grounded in meaningful reasons—you want to build a healthier dynamic, rooted in emotional independence and true vulnerability. That’s an admirable goal. However, would your ex be open to starting fresh with a stronger foundation? If she remains tied to old patterns, reconciliation might not be as smooth as you hope.

At the same time, your realization that casual dating and sex aren’t truly what you’re seeking is significant. It highlights that your focus is on depth, connection, and community rather than fleeting experiences. That speaks to a level of emotional maturity and self-awareness that will help guide your decision.

You wrote, “I hesitate with all huge decisions I make partly out of a fear of what I don’t know, or a fear that all of my feelings are incorrect and I will make a wrong decision.” This, I believe, is your greatest challenge—distrusting or doubting your own emotions. I wonder how that came about. Were your feelings as a child dismissed, ignored, or criticized?

anita

Dear Jack:

Your childhood story, invalidated emotions, silent treatments, even gaslighted, unfortunately it’s a common story, mine as well. Yet, it’s a heart breaking story for each and every child it happens to, and I am sorry 😞 that it’s your story too.

So many of us adults, of all ages, are hurt little boys and girls because we were not seen or validated.

Healing is about no longer repressing or suppressing our emotions,no longer rejecting them like others did, and instead, embracing them, giving them their due space within to breathe.

I am guessing you’ve been working on this in therapy?

Anita